CZ297065B6 - Hydrochlorid valacykloviru v bezvodé krystalické forme a zpusob jeho výroby - Google Patents

Hydrochlorid valacykloviru v bezvodé krystalické forme a zpusob jeho výroby Download PDF

Info

Publication number: CZ297065B6
Authority: CZ; Czechia
Prior art keywords: valaciclovir hydrochloride; valaciclovir; crystalline form; hydrochloride; weight
Prior art date: 1995-01-20

Application number

CZ0229497A

Other languages

Czech (cs)

English (en)

Other versions

CZ229497A3 (en

Inventor

Howard Carter@Barry

Muse Partin@Jane

Gregory Varlashkin@Peter

Augustus Winnike@Richard

Bayne Grubb@William III

Alan Conway@Gregory

George Lake@Philip

Michael Skinner@David

James Whatrup@David

Original Assignee

The Wellcome Foundation Limited

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1995-01-20

Filing date

1996-01-19

Publication date

2006-08-16

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=10768347&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CZ297065(B6) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1996-01-19 Application filed by The Wellcome Foundation Limited filed Critical The Wellcome Foundation Limited

1997-12-17 Publication of CZ229497A3 publication Critical patent/CZ229497A3/cs

2006-08-16 Publication of CZ297065B6 publication Critical patent/CZ297065B6/cs

Links

ZCDDBUOENGJMLV-QRPNPIFTSA-N Valacyclovir hydrochloride Chemical compound Cl.N1C(N)=NC(=O)C2=C1N(COCCOC(=O)[C@@H](N)C(C)C)C=N2 ZCDDBUOENGJMLV-QRPNPIFTSA-N 0.000 title claims description 71
238000000034 method Methods 0.000 title claims description 22
238000002360 preparation method Methods 0.000 title claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 37
239000000203 mixture Substances 0.000 claims description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
239000002904 solvent Substances 0.000 claims description 21
HDOVUKNUBWVHOX-QMMMGPOBSA-N Valacyclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCOC(=O)[C@@H](N)C(C)C)C=N2 HDOVUKNUBWVHOX-QMMMGPOBSA-N 0.000 claims description 18
229940093257 valacyclovir Drugs 0.000 claims description 16
238000000634 powder X-ray diffraction Methods 0.000 claims description 11
238000009826 distribution Methods 0.000 claims description 9
230000003381 solubilizing effect Effects 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
239000012458 free base Substances 0.000 claims description 6
150000002576 ketones Chemical class 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
150000003839 salts Chemical group 0.000 claims description 6
238000010586 diagram Methods 0.000 claims description 4
229940079593 drug Drugs 0.000 claims description 4
238000002156 mixing Methods 0.000 claims description 4
239000013078 crystal Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
239000013557 residual solvent Substances 0.000 claims description 2
206010019972 Herpes viral infections Diseases 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 5
PQGVTLQEKCJXKF-RGMNGODLSA-N ethyl (2s)-2-amino-3-methylbutanoate;hydron;chloride Chemical compound Cl.CCOC(=O)[C@@H](N)C(C)C PQGVTLQEKCJXKF-RGMNGODLSA-N 0.000 abstract 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
150000001875 compounds Chemical class 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
239000004480 active ingredient Substances 0.000 description 13
239000000843 powder Substances 0.000 description 13
-1 compound valaciclovir hydrochloride Chemical class 0.000 description 11
239000003826 tablet Substances 0.000 description 11
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 10
MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 9
229960004150 aciclovir Drugs 0.000 description 8
239000011928 denatured alcohol Substances 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
239000007787 solid Substances 0.000 description 8
KZSNJWFQEVHDMF-BYPYZUCNSA-N L-Valine Natural products CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 7
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
238000002441 X-ray diffraction Methods 0.000 description 6
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239000008187 granular material Substances 0.000 description 6
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229960004295 valine Drugs 0.000 description 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
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VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
208000036142 Viral infection Diseases 0.000 description 4
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238000005292 vacuum distillation Methods 0.000 description 4
208000009889 Herpes Simplex Diseases 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
241000124008 Mammalia Species 0.000 description 3
229920000168 Microcrystalline cellulose Polymers 0.000 description 3
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000002775 capsule Substances 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
239000000306 component Substances 0.000 description 3
239000010949 copper Substances 0.000 description 3
239000008358 core component Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000011521 glass Substances 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
235000019813 microcrystalline cellulose Nutrition 0.000 description 3
239000008108 microcrystalline cellulose Substances 0.000 description 3
229940016286 microcrystalline cellulose Drugs 0.000 description 3
229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
229940069328 povidone Drugs 0.000 description 3
230000005855 radiation Effects 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000002002 slurry Substances 0.000 description 3
238000003860 storage Methods 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
208000007514 Herpes zoster Diseases 0.000 description 2
241000701027 Human herpesvirus 6 Species 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
241000700605 Viruses Species 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000011324 bead Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000002512 chemotherapy Methods 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
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238000005070 sampling Methods 0.000 description 2
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229910002016 Aerosil® 200 Inorganic materials 0.000 description 1
208000031295 Animal disease Diseases 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000701022 Cytomegalovirus Species 0.000 description 1
206010011831 Cytomegalovirus infection Diseases 0.000 description 1
241000450599 DNA viruses Species 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
208000031886 HIV Infections Diseases 0.000 description 1
208000037357 HIV infectious disease Diseases 0.000 description 1
208000001688 Herpes Genitalis Diseases 0.000 description 1
206010019973 Herpes virus infection Diseases 0.000 description 1
241000175212 Herpesvirales Species 0.000 description 1
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XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical group C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
238000003109 Karl Fischer titration Methods 0.000 description 1
101000870363 Oryctolagus cuniculus Glutathione S-transferase Yc Proteins 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
229920003081 Povidone K 30 Polymers 0.000 description 1
229920003082 Povidone K 90 Polymers 0.000 description 1
208000005181 Varicella Zoster Virus Infection Diseases 0.000 description 1
208000000260 Warts Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
239000012752 auxiliary agent Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
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229940075894 denatured ethanol Drugs 0.000 description 1
150000004683 dihydrates Chemical group 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
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210000001035 gastrointestinal tract Anatomy 0.000 description 1
201000004946 genital herpes Diseases 0.000 description 1
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239000007937 lozenge Substances 0.000 description 1
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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208000003154 papilloma Diseases 0.000 description 1
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229920001223 polyethylene glycol Polymers 0.000 description 1
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229950008882 polysorbate Drugs 0.000 description 1
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230000002265 prevention Effects 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
239000008213 purified water Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
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239000004094 surface-active agent Substances 0.000 description 1
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239000006068 taste-masking agent Substances 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
241001430294 unidentified retrovirus Species 0.000 description 1
229940064636 valacyclovir hydrochloride Drugs 0.000 description 1
208000010531 varicella zoster infection Diseases 0.000 description 1
238000005303 weighing Methods 0.000 description 1
HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
229960002555 zidovudine Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Virology (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
Molecular Biology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Saccharide Compounds (AREA)

CZ0229497A 1995-01-20 1996-01-19 Hydrochlorid valacykloviru v bezvodé krystalické forme a zpusob jeho výroby CZ297065B6 (cs)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9501178.9A GB9501178D0 (en)	1995-01-20	1995-01-20	Guanine derivative
PCT/GB1996/000117 WO1996022291A1 (en)	1995-01-20	1996-01-19	Guanine derivative

Publications (2)

Publication Number	Publication Date
CZ229497A3 CZ229497A3 (en)	1997-12-17
CZ297065B6 true CZ297065B6 (cs)	2006-08-16

Family

ID=10768347

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CZ0229497A CZ297065B6 (cs)	1995-01-20	1996-01-19	Hydrochlorid valacykloviru v bezvodé krystalické forme a zpusob jeho výroby

Country Status (40)

Country	Link
US (1)	US6107302A (it)
EP (1)	EP0804436B1 (it)
JP (1)	JP3176633B2 (it)
KR (1)	KR100376074B1 (it)
CN (1)	CN1049893C (it)
AP (1)	AP662A (it)
AR (1)	AR002270A1 (it)
AT (1)	ATE302777T1 (it)
AU (1)	AU702794B2 (it)
BG (1)	BG63393B1 (it)
BR (1)	BR9606768A (it)
CA (1)	CA2210799C (it)
CY (1)	CY2531B1 (it)
CZ (1)	CZ297065B6 (it)
DE (1)	DE69635106T2 (it)
DK (1)	DK0804436T3 (it)
EA (1)	EA000364B1 (it)
EE (1)	EE03528B1 (it)
ES (1)	ES2248806T3 (it)
FI (1)	FI973063L (it)
GB (1)	GB9501178D0 (it)
GE (1)	GEP20001940B (it)
HR (1)	HRP960024B1 (it)
HU (1)	HU222993B1 (it)
IL (1)	IL116831A (it)
IN (1)	IN182468B (it)
IS (1)	IS2268B (it)
NO (1)	NO315558B1 (it)
NZ (1)	NZ298851A (it)
OA (1)	OA10499A (it)
PL (1)	PL182175B1 (it)
RO (1)	RO118693B1 (it)
RS (1)	RS49518B (it)
SI (1)	SI0804436T1 (it)
SK (1)	SK285329B6 (it)
TR (1)	TR199700656T1 (it)
UA (1)	UA46001C2 (it)
UY (1)	UY25779A1 (it)
WO (1)	WO1996022291A1 (it)
ZA (1)	ZA96449B (it)

Families Citing this family (61)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9501178D0 (en) *	1995-01-20	1995-03-08	Wellcome Found	Guanine derivative
EP0874631B1 (en) *	1996-01-19	2003-11-19	Glaxo Group Limited	Use of valaciclovir for the manufacture of a medicament for the treatment of genital herpes by a single daily application
IT1283447B1 (it) *	1996-07-18	1998-04-21	Ind Chimica Srl	Processo di preparazione del valaciclovir e relativi intermedi
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1996
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- 1996-01-19 DE DE69635106T patent/DE69635106T2/de not_active Expired - Lifetime
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- 1996-01-19 US US08/875,173 patent/US6107302A/en not_active Expired - Lifetime
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- 1996-01-19 SI SI9630717T patent/SI0804436T1/sl unknown
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- 1996-01-19 ZA ZA96449A patent/ZA96449B/xx unknown
- 1996-01-19 DK DK96900631T patent/DK0804436T3/da active
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- 1996-01-19 AU AU44539/96A patent/AU702794B2/en not_active Ceased
- 1996-01-19 KR KR1019970704916A patent/KR100376074B1/ko not_active Expired - Lifetime
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- 1996-01-19 CN CN96192662A patent/CN1049893C/zh not_active Expired - Fee Related
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- 1996-01-19 FI FI973063A patent/FI973063L/fi not_active Application Discontinuation
- 1996-01-19 UA UA97084268A patent/UA46001C2/uk unknown
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- 1996-01-19 PL PL96321326A patent/PL182175B1/pl not_active IP Right Cessation
- 1996-01-19 CZ CZ0229497A patent/CZ297065B6/cs not_active IP Right Cessation
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- 1996-01-19 HU HU9801836A patent/HU222993B1/hu not_active IP Right Cessation
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1997
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1999
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2005
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Also Published As

Publication number	Publication date
CY2531B1 (en)	2006-04-12
HUP9801836A3 (en)	1999-06-28
PL182175B1 (pl)	2001-11-30
IS2268B (is)	2007-07-15
TR199700656T1 (xx)	1998-03-21
MX9705462A (es)	1997-10-31
CA2210799C (en)	2008-06-10
JPH11503718A (ja)	1999-03-30
GEP20001940B (en)	2000-02-05
YU3396A (sh)	1998-12-23
NO315558B1 (no)	2003-09-22
WO1996022291A1 (en)	1996-07-25
CZ229497A3 (en)	1997-12-17
DK0804436T3 (da)	2005-12-27
SI0804436T1 (sl)	2006-02-28
IL116831A0 (en)	1996-05-14
SK285329B6 (sk)	2006-11-03
CA2210799A1 (en)	1996-07-25
EE9700175A (et)	1998-02-16
AP9701058A0 (en)	1997-10-31
DE69635106T2 (de)	2006-06-08
IN182468B (it)	1999-04-17
RO118693B1 (ro)	2003-09-30
PL321326A1 (en)	1997-12-08
AU702794B2 (en)	1999-03-04
JP3176633B2 (ja)	2001-06-18
UY25779A1 (es)	2000-08-21
AR002270A1 (es)	1998-03-11
KR19980701525A (ko)	1998-05-15
AP662A (en)	1998-08-19
BG63393B1 (bg)	2001-12-29
CN1049893C (zh)	2000-03-01
ZA96449B (en)	1996-08-07
FI973063A7 (fi)	1997-09-18
DE69635106D1 (de)	2005-09-29
FI973063L (fi)	1997-09-18
CN1179159A (zh)	1998-04-15
IL116831A (en)	1998-10-30
EE03528B1 (et)	2001-10-15
RS49518B (sr)	2006-10-27
NZ298851A (en)	1999-01-28
BR9606768A (pt)	1997-12-30
KR100376074B1 (ko)	2003-06-02
ES2248806T3 (es)	2006-03-16
HUP9801836A2 (hu)	1999-05-28
HRP960024A2 (en)	1997-10-31
BG101833A (bg)	1998-04-30
IS4527A (is)	1997-07-15
HRP960024B1 (en)	2005-08-31
ATE302777T1 (de)	2005-09-15
GB9501178D0 (en)	1995-03-08
AU4453996A (en)	1996-08-07
EP0804436B1 (en)	2005-08-24
EA000364B1 (ru)	1999-06-24
HU222993B1 (hu)	2004-01-28
NO973326D0 (no)	1997-07-18
NO973326L (no)	1997-09-16
EP0804436A1 (en)	1997-11-05
SK96597A3 (en)	1998-02-04
OA10499A (en)	2002-04-10
EA199700124A1 (ru)	1997-12-30
UA46001C2 (uk)	2002-05-15
US6107302A (en)	2000-08-22
FI973063A0 (fi)	1997-07-18

Legal Events

Date	Code	Title	Description
2000-06-30	PD00	Pending as of 2000-06-30 in czech republic
2011-08-24	MM4A	Patent lapsed due to non-payment of fee	Effective date: 20110119

Publication	Publication Date	Title
CZ297065B6 (cs)	2006-08-16	Hydrochlorid valacykloviru v bezvodé krystalické forme a zpusob jeho výroby
KR100412298B1 (ko)	2004-04-21	콜로이드이산화규소를함유하는발라시클로비르정제
CA2243237C (en)	2008-09-02	Use of valaciclovir for the manufacture of a medicament for the treatment of genital herpes by a single daily application
HK1003055B (en)	2006-02-03	Guanine derivative
HK1003055A1 (en)	1998-10-09	Guanine derivative
MXPA97005462A (en)	1998-07-03	Derived from guan
MXPA97005459A (en)	1998-07-03	Valaciclovir tablets containing silicon dioxide color